Patent FR-2788773-A1 (FR)
Title: Cationic methylene-dioxy- benzenes used as oxidation dye precursors in compositions for oxidation-dyeing of keratin fibres, contain at least one cationic group including quaternized cycles
Inventor: GENET ALAIN
IPC: C07D413/12
Filed: 1999-01-21
Abstract: New cationic methylene-dioxy-benzenes and their acid-addition salts are claimed.  The cationic methylene-dioxy-benzenes are of formula (I). Ra, Rb  = H, (1-6C)alkyl radical or hydroxy (1-6C)alkyl radical, or form together with C atom to which they are attached a saturated 5,6 or 7C cycle;  R1-R3  = H, halogen, Z, A', 1-6C alkyl , (1-6C)alkyl carbonyl, amino(1-6C)alkyl carbonyl, N-Z-amino-(1-6C) alkylcarbonyl, N-(1-6C)alkyl-amino-(1-6C) alkylcarbonyl, or N,N-di(1-6C)alkyl-amino-(1-6C) alkylcarbonyl, etc.; R6 = 1-6C alkyl, mono- hydroxy (1-6C) alkyl, polyhydroxy (2-6C) alkyl, Z, aryl (or benzyl)l, trifluoro-, mono(or poly)- hydroxy-, (1-6C)-alkoxy-, cyano-, carbamyl-, N-(or N,N) (1-6C)-(di) alkylcarbamyl- radicals, thiocarbamyl-, cyano-, carbamyl, N-(1-6C)alkyl-carbamyl or N,N-di (1-6C) alkyl carbamyl, (1-6C)-alkyl-carboxy-, (1-6C) alkyl carbonyl-, (1-6C)alkyl sulfinyl-, aminosulfonyl-, N-Z-aminosulfonyl-, N-(1-6C)alkyl-aminosulfonyl-, N,N-di(1-6C)alkyl-aminosulfonyl-, aminosulfonyl-, and amino- (1-6C)alkyl; where alkyl may be substituted with one or more hydroxy radicals and amine is substituted with one or two same or different radicals selected from (1-6C)alkyl- and mono(or poly)-hydroxy- (1-6C) (or 2-6C) alkyl, (1-6C)alkyl carbonyl (or sulfonyl)-, formyl-, or trifluoro-(1-6C) alkyl-carbonyl (or carboxy)- radicals, or carbamyl-, thiocarbamyl-, N (or N,N)- (1-6C) (di) alkyl carbamyl, or Z; or may also form, with N atom to which they are linked, a 5-6 links cycle which may be of C atoms or may contain one or more hetero-atoms; A = -NR4R5 or hydroxyl; A' = -NR4'R5' or hydroxyl; R4, R5, R4' and R5'  = , H, Z, 1-6C alkyl, mono- hydroxy (1-6C) alkyl, polyhydroxy (2-6C) alkyl, aryl (or benzyl) radical, trifluoro-, sulfo-, thiocarbamyl-, cyano-, carbamyl, N-(1-6C)alkyl-carbamyl or N,N-di (1-6C) alkyl carbamyl, (1-6C)-alkyl-carboxy-, (1-6C) alkyl carbonyl-, (1-6C)alkyl sulfinyl-, aminosulfonyl-, N-Z-aminosulfonyl-, N-(1-6C)alkyl-aminosulfonyl-, N,N-di(1-6C)alkyl-aminosulfonyl-, and amino- (1-6C)alkyl; where alkyl may be substituted with one or more hydroxy radicals and amine is substituted with one or two same or different radicals selected from (1-6C)alkyl- and mono(or poly)-hydroxy- (1-6C) (or 2-6C) alkyl radicals, (1-6C)alkyl carbonyl (or sulfonyl)-, formyl-, or trifluoro-(1-6C) alkyl-carbonyl (or carboxy)- radicals, or carbamyl-, thiocarbamyl-, N (or N,N)- (1-6C) (di) alkyl carbamyl, or  Z; or may also form, with N atom to which they are linked, a 5-6 links cycle which may be of C atoms or may contain one or more hetero-atoms;  Z = unsaturated cationic groups of formula (II) and (III), or saturated cationic groups of formula (IV);  D = (preferably 1-14C) linear or branched chain, which may be interrupted with one or more heteroatoms (N, O or S) and substituted with one or more hydroxyl or 1-6C alkoxy radicals, and may have one or more ketone groups; E,G, J, L and M = C, O, S or N atom; n = 0-4; m = 0-5; R = second group Z identical or different to first, halogen, hydroxyl radical, (1-6C) alkyl-, mono (or poly) hydroxy-, or cyano- (1-6C)alkyl radicals, nitro-, cyano-, 1-6C alkoxy-, tri(1-6C) silane (1-6C) alkyl-, amido-, aldehydo-, carboxyl-, thio-, (1-6C) alkyl carbonyl-, thio-(1-6C) alkyl-, (1-6C)alkyl-thio- and amino- radicals, with amino- radical protected with (1-6C)alkyl carbonyl- (or carbamyl, or sulfonyl) radicals, or groups NHR'' or NR''R''';  R'', R''' = (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl;  R7  = (1-6C) alkyl, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, benzyl radical, cyano-, tri(1-6C)alkyl silane-, alkoxy, carbamyl or (1-6C) alkyl carboxy- (1-6C) alkyl radical; or second Z group identical or different from the first;  R8-R10  = (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical, (1-6C) alkoxy-, cyano-, amido- or tri(1-6C)alkyl silane- (1-6C) alkyl, or amino-(1-6C)alkyl with amine protected by (1-6C) alkyl sulfonyl- or amido-, carboxy- or carbonyl, or two of R8-R10 radicals may form with N atom 5-6 links saturated cycle which may contain one or more hetero-atoms and may be substituted with halogen, hydroxyl, (1-6C) alkyll, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, 1-6C alkyl-thio- or alkoxy-, nitro-, cyano-, amido-, aldehydo-, carboxyl- or thio- radical, or cyano-, keto-, thio-, or tri-(1-6C)alkyl silane- (1-6C)alkyl radical, or amine radical, protected with (1-6C)alkyl carbonyl- (or sulfonyl) radical, or one of R8-R10 may represent second Z group identical or different from the first; R11 = (1-6C) alkyll, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, aryl or benzyl, amino-(1-6C) alkyl with amine optionally protected with (1-6C)alkyl carbonyl- (or sulfonyl); or carboxy-, cyano-, carbamyl-, trifluoro-, tri(1-6C)alkyl silane-, sulfonamido-, (1-6C) alkyl carboxy-, (1-6C)alkyl sulfinyl- (or sulfonyl-, or keto-)-, or N-(1-6C)alkyl carbamyl- (or sulfonamido-) (1-6C) alkyl; X = monovalent or divalent anion; a and y = 0-1. Independent claims are also included for: (1) the use of compounds (I) as precursors of oxidation-colorants in oxidation-dyeing compositions for keratinic fibres; (2) composition A for oxidation-dyeing of keratinic fibres, containing at least one compound (I), in amount 0.0005-12 (preferably 0.005-6) wt.%, and also 0.0005-12 wt.% of one or more oxidation bases, 0.0001-10 wt.% of one or more couplers and/or one or more direct colorants; (3) process of oxidation-dyeing of keratinic fibres (especially of human hair), comprising application of composition as claimed, for a period necessary to develop color, which is developed in result of contact with air oxygen, or produced at acidic, neutral or alkaline pH with the aid of oxidant-agent added at the application stage or present in oxidant composition B applied simultaneously or in sequence, separately from composition A; and (4) dyeing kit with separate compartments of which the first contains dye composition A as claimed and the second oxidant composition B.